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Chapter 16
Aldehydes & Ketones I: Nucleophilic Additions to the Carbonyl Group
25
Chemistry
Undergraduate 4
05/02/2011

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Term
Carbonyl group
Definition
A functional group consisting of a carbon atom doubly bonded to an oxygen atom, >C=O
Term
Aldehyde
Definition
A molecule containing a terminal carbonyl group, >C=O , that is attached to one hydrogen and one other carbon atom, with the general formula RCHO
Term
Ketone
Definition
A molecule containing an internal carbonyl group, >C=O , that is attached to two other carbon atoms, with the general formula RCOR
Term
Acyl group
Definition
A functional group consisting of a carbonyl group, >C=O, attached to an alkyl or aryl group, R-C(=O)- ; it is often added by reaction of a compound with a carboxylic acid derivative. Also called an alkanoyl group
Term
Formyl group
Definition
The -CHO group. Also called a methanoyl group
Term
Acetyl group
Definition
The -COCH3 group. Also called an ethanoyl group
Term
Nucleophilic addition
Definition
A reaction in which a nucleophile adds to a substrate containing a polar multiple bond between carbon and a heteroatom (such as a carbonyl or nitrile group); the nucleophile attacks the δ+ carbon, which initially forms an alkoxide ion intermediate that subsequently attacks an electrophile (such as H+ )
Term
Hemiacetal
Definition
The product of the nucleophilic addition of one molecule of an alcohol to an aldehyde or ketone; the hemiacetal has one alkoxy group, -OR, and one hydroxyl group, -OH, on the former carbonyl carbon atom. This derivative of a ketone is also called a hemiketal
Term
Aldehyde hydrate
Definition
The product of the nucleophilic addition of one molecule of water to an aldehyde; the hydrate has two hydroxyl groups, -OH, on the former carbonyl carbon atom; this product is a terminal gem-diol (1,1-diol)
Term
Acetal
Definition
The product of the nucleophilic addition of two molecules of an alcohol to an aldehyde or ketone, with loss of one molecule of water; the acetal has two alkoxy groups, -OR, on the former carbonyl carbon atom. This derivative of a ketone is also called a ketal
Term
Condensation reaction
Definition
A reaction that joins two molecules, with the loss of water or an alcohol. Also called a dehydration synthesis reaction when water is lost
Term
Protecting group
Definition
A group that is introduced into a molecule to protect a sensitive group, while the reaction is carried out at some other location in the molecule; the protecting group is later removed in a subsequent reaction
Term
Thiol
Definition
A molecule containing a sulfhydryl (mercapto) group, -SH, which is the sulfur analogue of an alcohol. Also called a mercaptan
Term
Thioacetal
Definition
A derivative of an aldehyde or ketone having two alkylthiol groups, -SR, in place of the carbonyl group, which is derived by adding two molar equivalents of a thiol
Term
Raney nickel
Definition
A finely divided, hydrogen-bearing form of nickel made by treating a nickel-aluminum alloy with strong sodium hydroxide; the aluminum in the alloy reacts to form hydrogen, leaving a finely divided nickel powder saturated with hydrogen. Raney nickel desulfurization of thioacetals will leave a reduced methylene group
Term
Imine
Definition
A compound with a carbon-nitrogen double bond, R2C=NR', formed by the reaction of a ketone or aldehyde with a primary amine; a substituted imine is often called a Schiff base
Term
Enamine
Definition
A vinyl amine, usually generated by the acid-catalyzed reaction of a secondary amine with an aldehyde or ketone, which has the general formula: R2C=C(NR2)R
Term
Oxime
Definition
A compound containing the -C=N-OH group, formed by the reaction of an aldehyde or ketone with hydroxylamine, NH2OH
Term
Hydrazone
Definition
A compound containing the -C=N-NH2 group, formed by the reaction of an aldehyde or ketone with hydrazine, NH2 NH2
Term
2,4-DNP derivative
Definition
A hydrazone formed by the reaction of an aldehyde or ketone with 2,4-dinitrophenylhydrazine
Term
Semicarbazone
Definition
A compound containing the -C=N-NH-CONH2 group, formed by the reaction of an aldehyde or ketone with semicarbazide, H2NCONHNH2
Term
Cyanohydrin
Definition
A compound with a hydroxyl group and a cyano group on the same carbon atom, R2C(OH)(CN), derived by adding HCN to an aldehyde or ketone
Term
Ylide
Definition
An electrically neutral molecule that has a negative carbon with an unshared electron pair adjacent to a positive heteroatom
Term
Wittig reaction
Definition
Reaction of an aldehyde or ketone with a phosphorus ylide to form an alkene
Term
Tollens test
Definition
A test for aldehydes and α-hydroxy ketones. Adding the Tollens reagent, Ag(NH3)2OH, which is a silver-ammonia complex, will give a carboxylate salt and a silver mirror on the inside of a glass container
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